JP7491938B2 - Organic electroluminescent device - Google Patents
Organic electroluminescent device Download PDFInfo
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- JP7491938B2 JP7491938B2 JP2021550580A JP2021550580A JP7491938B2 JP 7491938 B2 JP7491938 B2 JP 7491938B2 JP 2021550580 A JP2021550580 A JP 2021550580A JP 2021550580 A JP2021550580 A JP 2021550580A JP 7491938 B2 JP7491938 B2 JP 7491938B2
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- organic electroluminescent
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- 150000001875 compounds Chemical class 0.000 claims description 68
- 125000004432 carbon atom Chemical group C* 0.000 claims description 67
- 239000000463 material Substances 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 43
- 239000002019 doping agent Substances 0.000 claims description 34
- 230000000903 blocking effect Effects 0.000 claims description 28
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052751 metal Inorganic materials 0.000 claims description 16
- 239000002184 metal Substances 0.000 claims description 16
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
- 230000003111 delayed effect Effects 0.000 claims description 13
- 238000000151 deposition Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
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- 229910052709 silver Inorganic materials 0.000 claims description 5
- 239000004332 silver Substances 0.000 claims description 5
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 3
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- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002524 organometallic group Chemical group 0.000 claims description 3
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- 239000010948 rhodium Substances 0.000 claims description 3
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- 230000008021 deposition Effects 0.000 description 10
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 10
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 10
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 8
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- 229910052749 magnesium Inorganic materials 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 229930192474 thiophene Natural products 0.000 description 8
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 7
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 7
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 6
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
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- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 6
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 6
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- 125000001424 substituent group Chemical group 0.000 description 6
- 150000003852 triazoles Chemical class 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 5
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- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 5
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 5
- PJVZQNVOUCOJGE-CALCHBBNSA-N chembl289853 Chemical compound N1([C@H]2CC[C@H](O2)N2[C]3C=CC=CC3=C3C2=C11)C2=CC=C[CH]C2=C1C1=C3C(=O)N(C)C1=O PJVZQNVOUCOJGE-CALCHBBNSA-N 0.000 description 5
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- 230000007246 mechanism Effects 0.000 description 5
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- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 4
- OWQPOVKKUWUEKE-UHFFFAOYSA-N 1,2,3-benzotriazine Chemical compound N1=NN=CC2=CC=CC=C21 OWQPOVKKUWUEKE-UHFFFAOYSA-N 0.000 description 4
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 4
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- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 4
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 4
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- 239000007772 electrode material Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
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- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 2
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Description
本発明は有機電界発光素子(有機EL素子という)に関するものである。詳しくはオリゴピリジン化合物からなる有機電界発光素子用材料を使用した有機EL素子に関する。The present invention relates to an organic electroluminescent device (referred to as an organic EL device). More specifically, it relates to an organic EL device that uses an organic electroluminescent device material consisting of an oligopyridine compound.
有機EL素子に電圧を印加することで、陽極から正孔が、陰極からは電子がそれぞれ発光層に注入される。そして発光層において、注入された正孔と電子が再結合し、励起子が生成される。この際、電子スピンの統計則により、一重項励起子及び三重項励起子が1:3の割合で生成する。一重項励起子による発光を用いる蛍光発光型の有機EL素子は、内部量子効率は25%が限界であるといわれている。一方で三重項励起子による発光を用いる燐光発光型の有機EL素子は、一重項励起子から項間交差が効率的に行われた場合には、内部量子効率が100%まで高められることが知られている。
しかしながら、燐光発光型の有機EL素子に関しては、長寿命化が技術的な課題となっている。
By applying a voltage to the organic EL element, holes are injected from the anode and electrons are injected from the cathode into the light-emitting layer. In the light-emitting layer, the injected holes and electrons recombine to generate excitons. At this time, singlet excitons and triplet excitons are generated in a ratio of 1:3 according to the statistical law of electron spin. It is said that the internal quantum efficiency of a fluorescent organic EL element that uses emission from singlet excitons is limited to 25%. On the other hand, it is known that the internal quantum efficiency of a phosphorescent organic EL element that uses emission from triplet excitons can be increased to 100% if intersystem crossing from singlet excitons is efficiently performed.
However, for phosphorescent organic EL elements, extending their lifespan is a technical challenge.
最近では、遅延蛍光を利用した高効率の有機EL素子の開発がなされている。例えば特許文献1には、遅延蛍光のメカニズムの一つであるTTF(Triplet-Triplet Fusion)機構を利用した有機EL素子が開示されている。TTF機構は2つの三重項励起子の衝突によって一重項励起子が生成する現象を利用するものであり、理論上内部量子効率を40%まで高められると考えられている。しかしながら、燐光発光型の有機EL素子と比較すると効率が低いため、更なる効率の改良が求められている。
特許文献2では、TADF(Thermally Activated Delayed Fluorescence)機構を利用した有機EL素子が開示されている。TADF機構は一重項準位と三重項準位のエネルギー差が小さい材料において三重項励起子から一重項励起子への逆項間交差が生じる現象を利用するものであり、理論上内部量子効率を100%まで高められると考えられている。しかしながら、燐光発光型素子と同様に寿命特性の更なる改善が求められている。
Recently, highly efficient organic EL elements utilizing delayed fluorescence have been developed. For example,
特許文献3、4ではビスカルバゾール化合物を混合ホストとして使用することを開示している。
特許文献5ではインドロカルバゾール化合物を含む複数のホストを予備混合したホスト材料の使用を開示している。
特許文献6ではインドロカルバゾール化合物を熱活性化遅延蛍光発光ドーパント材料として使用することを開示している。
特許文献7ではビピリジン化合物について、ホスト材料としての使用を開示している。
特許文献8ではターピリジン化合物について、ホスト材料としての使用を開示している。
特許文献9ではクアテルピリジン化合物について、ホスト材料としての使用を開示している。
しかしながら、いずれも十分なものとは言えず、更なる改良が望まれている。
Patent Document 8 discloses the use of a terpyridine compound as a host material.
Patent Document 9 discloses the use of a quaterpyridine compound as a host material.
However, none of these methods are sufficient, and further improvements are desired.
有機EL素子をフラットパネルディスプレイ等の表示素子、または光源に応用するためには素子の発光効率を改善すると同時に駆動時の安定性を十分に確保する必要がある。本発明は、低駆動電圧でありながら高効率かつ高い駆動安定性を有した有機EL素子とそれに適した有機電界発光素子用材料を提供することを目的とする。In order to apply organic EL elements to display elements such as flat panel displays, or as light sources, it is necessary to improve the luminous efficiency of the elements while at the same time ensuring sufficient stability during operation. The object of the present invention is to provide an organic EL element that has high efficiency and high operating stability while requiring a low operating voltage, and a material suitable for such an organic electroluminescent element.
本発明者らは、鋭意検討した結果、特定のオリゴピリジン化合物を第1ホストとして用いることで優れた特性を示す有機EL素子となることを見出し、本発明を完成するに至った。As a result of extensive research, the inventors discovered that the use of a specific oligopyridine compound as the first host results in an organic EL element that exhibits excellent characteristics, and thus completed the present invention.
本発明は、対向する陽極と陰極の間に、1つ以上の発光層を含む有機電界発光素子において、少なくとも1つの発光層が、下記一般式(1)で表される化合物から選ばれる第1ホストと、下記一般式(2)、一般式(3)、一般式(4)又は一般式(5)で表される化合物から選ばれる第2ホストを含有することを特徴とする有機EL素子である。
ここで、L1~L3は単結合、置換若しくは未置換の炭素数6~30の芳香族炭化水素基、又はそれらが2~10連結してなる連結芳香族基を示し、R1~R7は独立に、水素、重水素、炭素数1~10の脂肪族炭化水素基、置換若しくは未置換の炭素数6~10の芳香族炭化水素基又は炭素数3~12の芳香族複素環基である。a、b、cは、繰り返し数を表し、a+b≧1である。各々独立して0~3の整数を表す。p,q,r,s,t,u,vは置換数を表し、各々独立して1~3の整数を表す。 Here, L 1 to L 3 represent a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a linked aromatic group formed by linking 2 to 10 of these, and R 1 to R 7 are independently hydrogen, deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aromatic heterocyclic group having 3 to 12 carbon atoms. a, b, and c represent the number of repetitions, and a+b≧1. Each independently represents an integer of 0 to 3. p, q, r, s, t, u, and v represent the number of substitutions, and each independently represents an integer of 1 to 3.
上記一般式(1)、一般式(2)、一般式(3)、一般式(4)又は一般式(5)の好ましい態様を次に示す。
一般式(2)が、下記式(6)であること。
The general formula (2) is the following formula (6).
一般式(3)が、下記式(7)又は式(8)であること。
一般式(4)において、少なくとも1つの式(c1)又は式(c2)で表される結合構造を有すること。
ここで、R13は一般式(4)と同意である。 In general formula (4), at least one bond structure represented by formula (c1) or formula (c2) is present.
Here, R 13 has the same meaning as in formula (4).
一般式(1)が、下記式(9)~(11)のいずれかであること。
上記有機電界発光素子の好ましい態様を次に示す。
第1ホストと第2ホストの合計に対し、第1ホストの割合が20wt%を超え、55wt%未満であること。
発光性ドーパント材料が、ルテニウム、ロジウム、パラジウム、銀、レニウム、オスミウム、イリジウム、白金及び金からなる群れから選ばれる少なくとも一つの金属を含む有機金属錯体であること、又は熱活性化遅延蛍光発光ドーパント材料であること。
発光層と隣接して正孔阻止層を設け、該正孔阻止層中に一般式(1)で表される化合物を含有させること。
Preferred embodiments of the organic electroluminescent device are as follows.
The ratio of the first host to the total of the first host and the second host is more than 20 wt% and less than 55 wt%.
The luminescent dopant material is an organometallic complex containing at least one metal selected from the group consisting of ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold, or is a thermally activated delayed fluorescent dopant material.
A hole blocking layer is provided adjacent to the light emitting layer, and the hole blocking layer contains a compound represented by formula (1).
また、本発明は上記の有機電界発光素子を製造するに当たり、第1ホストと第2ホストを混合して予備混合物としたのち、これを含むホスト材料を蒸着させて発光層を形成させる工程を有することを特徴とする有機電界発光素子の製造方法である。In addition, the present invention relates to a method for producing the above-mentioned organic electroluminescent element, which is characterized by having a process for mixing a first host and a second host to prepare a preliminary mixture, and then evaporating a host material containing the preliminary mixture to form an emitting layer.
上記有機電界発光素子の製造方法において、第1ホストと第2ホストの50%重量減少温度の差が20℃以内であることが適する。In the manufacturing method of the above organic electroluminescent device, it is suitable that the difference in 50% weight loss temperature between the first host and the second host is within 20°C.
素子特性向上のためには、有機層に使用する材料の電荷に対する耐久性が高いことが必要であり、特に発光層においては周辺層への励起子及び電荷の漏れを抑えることが重要である。この電荷/励起子の漏れ抑制には、発光層中における発光領域の偏りの改善が有効で、そのためには発光層への両電荷(電子/正孔)注入量若しくは発光層中における両電荷輸送量を好ましい範囲に制御することが必要である。
ここで、本発明で用いられる式(1)で表されるオリゴピリジン化合物は、ピリジン環が複数結合し、それらに二つ以上のカルバゾール環が結合した構造を有する。有機層に使用する材料の両電荷注入輸送能は、材料の分子軌道のエネルギー準位及び分子間の相互作用の大きさにより大きく左右される。オリゴピリジン化合物は、特に電子注入輸送能が高いがカルバゾール環の導入により、その立体障害効果からオリゴピリジン部位同士の近接を抑えることができる。そして、ピリジン環基の置換基種や結合位置を変えることで発光層への電子注入輸送への寄与の大きな分子軌道の分子間相互作用を高いレベルで制御できる。
一方で、一般式(2)~(5)で表されるカルバゾール化合物は、特に正孔注入輸送能が高く、カルバゾール環の結合様式や該骨格への置換基の種類・数を変えることで正孔注入輸送性が高いレベルで制御できる。そこで、上記オリゴピリジン化合物とカルバゾール化合物を混合して用いることで、有機層への両電荷注入量を好ましい範囲に調整でき、より良好な素子特性が期待できる。特に、遅延蛍光発光EL素子や燐光発光EL素子の場合にあっては、発光層で生成する励起エネルギーを閉じ込めるのに十分高い最低励起三重項エネルギーを有していることから、発光層内からのエネルギー流出がなく、低電圧で高効率かつ長寿命を達成できる。
To improve device characteristics, it is necessary that the materials used in the organic layers have high durability against electric charges, and it is particularly important to suppress the leakage of excitons and electric charges to the surrounding layers in the light-emitting layer. To suppress the leakage of electric charges/excitons, it is effective to improve the bias of the light-emitting region in the light-emitting layer, and for this purpose, it is necessary to control the amount of both electric charges (electrons/holes) injected into the light-emitting layer or the amount of both electric charges transported in the light-emitting layer within a preferred range.
Here, the oligopyridine compound represented by formula (1) used in the present invention has a structure in which a plurality of pyridine rings are bonded to which two or more carbazole rings are bonded. The charge injection and transport ability of the material used in the organic layer is greatly influenced by the energy level of the molecular orbital of the material and the magnitude of the intermolecular interaction. The oligopyridine compound has particularly high electron injection and transport ability, but the introduction of the carbazole ring can suppress the proximity of the oligopyridine moieties due to the steric hindrance effect. In addition, by changing the type of substituent or the bond position of the pyridine ring group, the intermolecular interaction of the molecular orbital that contributes greatly to the injection and transport of electrons to the light-emitting layer can be controlled at a high level.
On the other hand, the carbazole compounds represented by the general formulas (2) to (5) have particularly high hole injection and transport properties, and the hole injection and transport properties can be controlled at a high level by changing the bonding style of the carbazole ring and the type and number of substituents on the skeleton. Therefore, by using a mixture of the above oligopyridine compound and the carbazole compound, the amount of both charges injected into the organic layer can be adjusted to a preferred range, and better device characteristics can be expected. In particular, in the case of delayed fluorescent EL devices and phosphorescent EL devices, since they have a minimum excited triplet energy that is high enough to trap the excitation energy generated in the emitting layer, there is no energy outflow from the emitting layer, and high efficiency and long life can be achieved at a low voltage.
本発明の有機EL素子は、基板上に、陽極、有機層及び陰極が積層された構造を有し、この有機層の少なくとも1層に、上記の有機電界発光素子用材料を含む。
この有機EL素子は、対向する陽極と陰極の間に複数の層からなる有機層を有するが、複数の層の少なくとも1層は、発光層であり、発光層は複数あってもよい。そして、発光層の少なくとも一つは、第1ホストと、第2ホスト及び発光性ドーパント材料を含有する蒸着層からなる発光層である。
The organic EL device of the present invention has a structure in which an anode, an organic layer, and a cathode are laminated on a substrate, and at least one of the organic layers contains the above-mentioned material for organic electroluminescent devices.
This organic EL device has a plurality of organic layers between an anode and a cathode facing each other, at least one of which is an emitting layer (there may be a plurality of emitting layers), and at least one of the emitting layers is an emitting layer formed by deposition of a first host, a second host, and a luminescent dopant material.
上記発光層に含まれる第1ホストは上記一般式(1)で表される化合物から選ばれ、第2ホストは上記一般式(2)、一般式(3)、一般式(4)又は一般式(5)で表される化合物から選ばれることを特徴とする有機電界発光素子。An organic electroluminescent device, characterized in that the first host contained in the light-emitting layer is selected from the compounds represented by the above general formula (1), and the second host is selected from the compounds represented by the above general formula (2), general formula (3), general formula (4) or general formula (5).
第1ホストは、上記一般式(1)で表されるオリゴピリジン化合物から選ばれる。The first host is selected from oligopyridine compounds represented by the above general formula (1).
一般式(1)において、R1~R7は独立に、水素、重水素、炭素数1~10の脂肪族炭化水素基、炭素数6~30の芳香族炭化水素基又は炭素数3~12の芳香族複素環基を示す。好ましくは、炭素数1~8の脂肪族炭化水素基、フェニル基、又は炭素数3~12の芳香族複素環基である。より好ましくは、炭素数1~6の脂肪族炭化水素基、フェニル基、又はカルバゾール環基である。
本明細書において、芳香族炭化水素基、芳香族複素環基及びこれらの芳香族環が単結合で連結して生じる連結芳香族基は、特に無置換と断りがない場合は、置換基を有し得ると解される。脂肪族炭化水素基も同様である。
In general formula (1), R 1 to R 7 independently represent hydrogen, deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or an aromatic heterocyclic group having 3 to 12 carbon atoms. An aliphatic hydrocarbon group having 1 to 8 carbon atoms, a phenyl group, or an aromatic heterocyclic group having 3 to 12 carbon atoms is preferred. An aliphatic hydrocarbon group having 1 to 6 carbon atoms, a phenyl group, or a carbazole ring group is more preferred.
In this specification, aromatic hydrocarbon groups, aromatic heterocyclic groups, and linked aromatic groups formed by linking these aromatic rings with a single bond are understood to be substituted unless otherwise specified as being unsubstituted. The same applies to aliphatic hydrocarbon groups.
上記脂肪族炭化水素基の具体例としては、メチル、エチル、プロピル、ブチル、ペンチル、へキシル、ヘプチル、オクチル、ノニル、デシル等が挙げられる。好ましくは、炭素数1~4のアルキル基である。 Specific examples of the aliphatic hydrocarbon group include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, etc. Preferred are alkyl groups having 1 to 4 carbon atoms.
上記芳香族炭化水素基、又は芳香族複素環基の具体例としては、ベンゼン、ナフタレン、ピリジン、ピリミジン、トリアジン、チオフェン、イソチアゾール、チアゾール、ピリダジン、ピロール、ピラゾール、イミダゾール、トリアゾール、チアジアゾール、ピラジン、フラン、イソキサゾール、オキサゾール、オキサジアゾール、キノリン、イソキノリン、キノキサリン、キナゾリン、オキサジアゾール、チアジアゾール、ベンゾトリアジン、フタラジン、テトラゾール、インドール、ベンゾフラン、ベンゾチオフェン、ベンゾオキサゾール、ベンゾチアゾール、インダゾール、ベンズイミダゾール、ベンゾトリアゾール、ベンゾイソチアゾール、ベンゾチアジアゾール、ジベンゾフラン、ジベンゾチオフェン、ジベンゾセレノフェン、又はカルバゾールから1個のHをとって生じる芳香族基が挙げられる。好ましくは、ベンゼン、ピリジン、ピリミジン、トリアジン、チオフェン、イソチアゾール、チアゾール、ピリダジン、ピロール、ピラゾール、イミダゾール、トリアゾール、チアジアゾール、ピラジン、フラン、イソキサゾール、オキサゾール、オキサジアゾール、キノリン、イソキノリン、キノキサリン、キナゾリン、オキサジアゾール、チアジアゾール、ベンゾトリアジン、フタラジン、テトラゾール、インドール、ベンゾフラン、ベンゾチオフェン、ベンゾオキサゾール、ベンゾチアゾール、インダゾール、ベンズイミダゾール、ベンゾトリアゾール、ベンゾイソチアゾール、又はベンゾチアジアゾールから生じる芳香族基が挙げられる。より好ましくは、ベンゼン、ピリジン、ピリミジン、トリアジン、チオフェン、イソチアゾール、チアゾール、ピリダジン、ピロール、ピラゾール、イミダゾール、トリアゾール、チアジアゾール、ピラジン、フラン、イソキサゾール、オキサゾール、又はオキサジアゾールから生じる芳香族基が挙げられる。 Specific examples of the above aromatic hydrocarbon groups or aromatic heterocyclic groups include aromatic groups formed by removing one H from benzene, naphthalene, pyridine, pyrimidine, triazine, thiophene, isothiazole, thiazole, pyridazine, pyrrole, pyrazole, imidazole, triazole, thiadiazole, pyrazine, furan, isoxazole, oxadiazole, quinoline, isoquinoline, quinoxaline, quinazoline, oxadiazole, thiadiazole, benzotriazine, phthalazine, tetrazole, indole, benzofuran, benzothiophene, benzoxazole, benzothiazole, indazole, benzimidazole, benzotriazole, benzisothiazole, benzothiadiazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, or carbazole. Preferred are aromatic groups derived from benzene, pyridine, pyrimidine, triazine, thiophene, isothiazole, thiazole, pyridazine, pyrrole, pyrazole, imidazole, triazole, thiadiazole, pyrazine, furan, isoxazole, oxazole, oxadiazole, quinoline, isoquinoline, quinoxaline, quinazoline, oxadiazole, thiadiazole, benzotriazine, phthalazine, tetrazole, indole, benzofuran, benzothiophene, benzoxazole, benzothiazole, indazole, benzimidazole, benzotriazole, benzisothiazole, or benzothiadiazole. More preferred are aromatic groups derived from benzene, pyridine, pyrimidine, triazine, thiophene, isothiazole, thiazole, pyridazine, pyrrole, pyrazole, imidazole, triazole, thiadiazole, pyrazine, furan, isoxazole, oxazole, or oxadiazole.
L1~L3は独立に、単結合、置換若しくは未置換の炭素数6~10の芳香族炭化水素基、又はそれらが2~10連結してなる連結芳香族基を示す。芳香族炭化水素基の好ましい例は、ベンゼン、ナフタレンから生じる2価の基が挙げられる。連結芳香族基の好ましい例は、ビフェニル、ターフェニルから生じる2価の基が挙げられる。 L 1 to L 3 each independently represent a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, or a linked aromatic group formed by linking 2 to 10 of these. Preferred examples of the aromatic hydrocarbon group include divalent groups derived from benzene and naphthalene. Preferred examples of the linked aromatic group include divalent groups derived from biphenyl and terphenyl.
a、b、cは、繰り返し数を表し、各々独立して0~3の整数を表し、好ましくは0又は1の整数である。但し、a+b≧1である。
p~vは置換数を表し、各々独立して1~3の整数を表し、好ましくは1又は2の整数である。
a, b, and c represent the number of repetitions, and each independently represents an integer of 0 to 3, and preferably an integer of 0 or 1, provided that a+b≧1.
p to v represent the number of substitutions, each independently representing an integer of 1 to 3, preferably an integer of 1 or 2.
一般式(1)で表される化合物の好ましい態様として、上記一般式(9)~(11)のいずれかで表される化合物がある。一般式(9)~(11)において、一般式(1)と共通する記号は同じ意味を有する。A preferred embodiment of the compound represented by general formula (1) is a compound represented by any of the above general formulas (9) to (11). In general formulas (9) to (11), symbols common to general formula (1) have the same meanings.
一般式(1)で表される化合物の具体的な例を以下に示すが、これら例示化合物に限定されるものではない。 Specific examples of compounds represented by general formula (1) are shown below, but are not limited to these exemplified compounds.
第2ホストは、上記一般式(2)、(3)、(4)又は(5)で表される化合物から選ばれる。The second host is selected from compounds represented by general formula (2), (3), (4) or (5) above.
第2ホストとなる一般式(2)、及びその好ましい態様である式(6)について、説明する。一般式(2)と式(6)において、共通する記号は同じ意味を有する。
R8とR9は独立に、水素、炭素数6~14の芳香族炭化水素基、または該芳香族炭化水素基の芳香族環が2個連結した連結芳香族基を表す。好ましくは、水素、炭素数6~12の芳香族炭化水素基であり、より好ましくは炭素数6~10の芳香族炭化水素基である。R8が水素であること、又はR8が水素であって、R9が上記芳香族炭化水素基、又は連結芳香族基であることは好ましい態様である。
The general formula (2) serving as the second host and its preferred embodiment, formula (6), will be described below. In general formula (2) and formula (6), the common symbols have the same meanings.
R8 and R9 independently represent hydrogen, an aromatic hydrocarbon group having 6 to 14 carbon atoms, or a linked aromatic group in which two aromatic rings of the aromatic hydrocarbon group are linked together. Preferred are hydrogen and an aromatic hydrocarbon group having 6 to 12 carbon atoms, and more preferred are aromatic hydrocarbon groups having 6 to 10 carbon atoms. In a preferred embodiment, R8 is hydrogen, or R8 is hydrogen and R9 is the aromatic hydrocarbon group or linked aromatic group.
R8とR9が芳香族炭化水素基、連結芳香族基である場合の具体例は、ベンゼン、ナフタレン、アントラセン、フェナントレン、フルオレン、ビフェニル等の芳香族炭化水素、又はこれら芳香族炭化水素の芳香族環が2個連結した化合物からHを1個とって生じる芳香族基又は連結芳香族基が挙げられる。好ましくは、ベンゼン、ナフタレン、アントラセン、フェナントレンから生じる芳香族基又はこれらの芳香族基が2個連結した連結芳香族基が挙げられ、より好ましくはベンゼン、ナフタレン、フェナントレン又はビフェニルから生じる芳香族基である。R8とR9がフェニル基であることが更に好ましい。
R8とR9は水素であってもよいが、その場合は、一方は上記芳香族基又は連結芳香族基であることがよい。R8が水素であって、R9がフェニル基であることが更に好ましい。また、上記芳香族基又は連結芳香族基は置換基を有してもよく、好ましい置換基は炭素数1~12アルキル基又は炭素数1~12アルコキシ基である。
Specific examples of R8 and R9 being aromatic hydrocarbon groups or linked aromatic groups include aromatic hydrocarbons such as benzene, naphthalene, anthracene, phenanthrene, fluorene, and biphenyl, or aromatic groups or linked aromatic groups resulting from removing one H from compounds in which two aromatic rings of these aromatic hydrocarbons are linked.Preferably, aromatic groups resulting from benzene, naphthalene, anthracene, and phenanthrene, or linked aromatic groups in which two of these aromatic groups are linked, are mentioned, and more preferably, aromatic groups resulting from benzene, naphthalene, phenanthrene, or biphenyl.It is even more preferable that R8 and R9 are phenyl groups.
R8 and R9 may be hydrogen, in which case one of them may be the above aromatic group or linking aromatic group. It is more preferable that R8 is hydrogen and R9 is a phenyl group. The above aromatic group or linking aromatic group may have a substituent, and the preferred substituent is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.
L4、L5は、フェニレン基であるが、フェニレン基はo-フェニレン基、m-フェニレン基及びp-フェニレン基のいずれでもよい。好ましくは、p-フェニレン基又はm-フェニレン基である。そして、L4とL5が相違することが好ましい。この場合、R8とR9が水素である場合は、フェニル基として扱い、フェニレン基とは相違するとする。 L4 and L5 are phenylene groups, which may be any of o-phenylene, m-phenylene and p-phenylene groups. Preferably, they are p-phenylene or m-phenylene groups. It is preferable that L4 and L5 are different. In this case, when R8 and R9 are hydrogen, they are treated as phenyl groups and are different from phenylene groups.
一般式(2)、(6)で表される化合物の具体的な例を以下に示すが、これら例示化合物に限定されるものではない。 Specific examples of compounds represented by general formulas (2) and (6) are shown below, but are not limited to these exemplified compounds.
次に、上記一般式(3)について説明する。
一般式(3)において、環Cは式(3a)で表される複素環であり、環Cは隣接する環と任意の位置で縮合する。
R10~R12は独立に水素、重水素、炭素数1~10の脂肪族炭化水素基、炭素数6~10の芳香族炭化水素基又は炭素数3~12の芳香族複素環基である。好ましくは、炭素数1~8の脂肪族炭化水素基、フェニル基、又は炭素数3~9の芳香族複素環基である。より好ましくは、炭素数1~6の脂肪族炭化水素基、フェニル基、又は炭素数3~6の芳香族複素環基である。
Next, the above general formula (3) will be described.
In general formula (3), ring C is a heterocycle represented by formula (3a), and ring C is condensed with the adjacent ring at any position.
R 10 to R 12 are independently hydrogen, deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aromatic heterocyclic group having 3 to 12 carbon atoms. An aliphatic hydrocarbon group having 1 to 8 carbon atoms, a phenyl group, or an aromatic heterocyclic group having 3 to 9 carbon atoms is preferred. An aliphatic hydrocarbon group having 1 to 6 carbon atoms, a phenyl group, or an aromatic heterocyclic group having 3 to 6 carbon atoms is more preferred.
上記脂肪族炭化水素基の具体例としては、メチル、エチル、プロピル、ブチル、ペンチル、へキシル、ヘプチル、オクチル、ノニル、デシル等が挙げられる。好ましくは、炭素数1~4のアルキル基である。 Specific examples of the aliphatic hydrocarbon group include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, etc. Preferred are alkyl groups having 1 to 4 carbon atoms.
上記芳香族炭化水素基、又は芳香族複素環基の具体例としては、ベンゼン、ナフタレン、ピリジン、ピリミジン、トリアジン、チオフェン、イソチアゾール、チアゾール、ピリダジン、ピロール、ピラゾール、イミダゾール、トリアゾール、チアジアゾール、ピラジン、フラン、イソキサゾール、オキサゾール、オキサジアゾール、キノリン、イソキノリン、キノキサリン、キナゾリン、オキサジアゾール、チアジアゾール、ベンゾトリアジン、フタラジン、テトラゾール、インドール、ベンゾフラン、ベンゾチオフェン、ベンゾオキサゾール、ベンゾチアゾール、インダゾール、ベンズイミダゾール、ベンゾトリアゾール、ベンゾイソチアゾール、ベンゾチアジアゾール、ジベンゾフラン、ジベンゾチオフェン、ジベンゾセレノフェン、又はカルバゾールから1個のHをとって生じる芳香族基が挙げられる。好ましくは、ベンゼン、ピリジン、ピリミジン、トリアジン、チオフェン、イソチアゾール、チアゾール、ピリダジン、ピロール、ピラゾール、イミダゾール、トリアゾール、チアジアゾール、ピラジン、フラン、イソキサゾール、オキサゾール、オキサジアゾール、キノリン、イソキノリン、キノキサリン、キナゾリン、オキサジアゾール、チアジアゾール、ベンゾトリアジン、フタラジン、テトラゾール、インドール、ベンゾフラン、ベンゾチオフェン、ベンゾオキサゾール、ベンゾチアゾール、インダゾール、ベンズイミダゾール、ベンゾトリアゾール、ベンゾイソチアゾール、又はベンゾチアジアゾールから生じる芳香族基が挙げられる。より好ましくは、ベンゼン、ピリジン、ピリミジン、トリアジン、チオフェン、イソチアゾール、チアゾール、ピリダジン、ピロール、ピラゾール、イミダゾール、トリアゾール、チアジアゾール、ピラジン、フラン、イソキサゾール、オキサゾール、又はオキサジアゾールから生じる芳香族基が挙げられる。 Specific examples of the above aromatic hydrocarbon groups or aromatic heterocyclic groups include aromatic groups formed by removing one H from benzene, naphthalene, pyridine, pyrimidine, triazine, thiophene, isothiazole, thiazole, pyridazine, pyrrole, pyrazole, imidazole, triazole, thiadiazole, pyrazine, furan, isoxazole, oxadiazole, quinoline, isoquinoline, quinoxaline, quinazoline, oxadiazole, thiadiazole, benzotriazine, phthalazine, tetrazole, indole, benzofuran, benzothiophene, benzoxazole, benzothiazole, indazole, benzimidazole, benzotriazole, benzisothiazole, benzothiadiazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, or carbazole. Preferred are aromatic groups derived from benzene, pyridine, pyrimidine, triazine, thiophene, isothiazole, thiazole, pyridazine, pyrrole, pyrazole, imidazole, triazole, thiadiazole, pyrazine, furan, isoxazole, oxazole, oxadiazole, quinoline, isoquinoline, quinoxaline, quinazoline, oxadiazole, thiadiazole, benzotriazine, phthalazine, tetrazole, indole, benzofuran, benzothiophene, benzoxazole, benzothiazole, indazole, benzimidazole, benzotriazole, benzisothiazole, or benzothiadiazole. More preferred are aromatic groups derived from benzene, pyridine, pyrimidine, triazine, thiophene, isothiazole, thiazole, pyridazine, pyrrole, pyrazole, imidazole, triazole, thiadiazole, pyrazine, furan, isoxazole, oxazole, or oxadiazole.
L6は独立に単結合、炭素数6~10の芳香族炭化水素基又は炭素数3~12の芳香族複素環基又はそれらが2~10連結してなる連結芳香族基である。芳香族炭化水素基又は芳香族複素環基の好ましい例は、これらの基が2価の基であることを除きR10がこれらの基である場合と同様である。
Ar1は炭素数6~10の芳香族炭化水素基又は炭素数3~12の芳香族複素環基である。芳香族炭化水素基又は芳香族複素環基の好ましい例は、これらの基が2価の基であることを除き、R10がこれらの基である場合と同様である。
f、g、hは、各々独立して0~3の整数を表す。
L6 is independently a single bond, an aromatic hydrocarbon group having 6 to 10 carbon atoms, an aromatic heterocyclic group having 3 to 12 carbon atoms, or a linked aromatic group formed by linking 2 to 10 of them. Preferred examples of the aromatic hydrocarbon group or aromatic heterocyclic group are the same as those when R10 is these groups, except that these groups are divalent groups.
Ar 1 is an aromatic hydrocarbon group having 6 to 10 carbon atoms or an aromatic heterocyclic group having 3 to 12 carbon atoms. Preferred examples of the aromatic hydrocarbon group or aromatic heterocyclic group are the same as those when R 10 is these groups, except that these groups are divalent groups.
f, g, and h each independently represent an integer of 0 to 3.
一般式(3)で表される化合物が、上記式(7)又は式(8)で表される化合物であることが好ましい。
式(7)又は式(8)において、環B、R10~R13、Ar1、x、yは一般式(3)と同意である。
The compound represented by the general formula (3) is preferably a compound represented by the above formula (7) or formula (8).
In formula (7) or (8), ring B, R 10 to R 13 , Ar 1 , x and y are the same as those in formula (3).
一般式(3)で表されるインドロカルバゾール化合物の具体例を以下に示すが、これらに限定されるものではない Specific examples of the indolocarbazole compound represented by general formula (3) are shown below, but are not limited to these.
次に、上記一般式(4)について説明する。
一般式(4)において、L7は炭素数6~30の芳香族炭化水素基又は炭素数3~30の芳香族複素環基、又はこれらの芳香族環が連結した連結芳香族基である。連結芳香族基は、芳香族炭化水素基又は芳香族複素環基の芳香族環が単結合で2~10個連結した構造の基である。
L7はm価の基であり、芳香族炭化水素基、芳香族複素環基、又は連結芳香族基は、置換基を有してもよい。
ここで、L7はカルバゾール環を含む基であることはない。
Next, the above general formula (4) will be described.
In general formula (4), L7 is an aromatic hydrocarbon group having 6 to 30 carbon atoms, an aromatic heterocyclic group having 3 to 30 carbon atoms, or a linked aromatic group in which these aromatic rings are linked. The linked aromatic group is a group having a structure in which 2 to 10 aromatic rings of an aromatic hydrocarbon group or an aromatic heterocyclic group are linked by single bonds.
L7 is an m-valent group, and the aromatic hydrocarbon group, aromatic heterocyclic group, or linking aromatic group may have a substituent.
Here, L7 is not a group containing a carbazole ring.
芳香族炭化水素基又は芳香族複素環基の具体例としては、ベンゼン、ペンタレン、インデン、ナフタレン、アズレン、ヘプタレン、オクタレン、インダセン、アセナフチレン、フェナレン、フェナンスレン、アントラセン、トリンデン、フルオランテン、アセフェナントリレン、アセアントリレン、トリフェニレン、ピレン、クリセン、テトラフェン、テトラセン、プレイアデン、ピセン、ペリレン、ペンタフェン、ペンタセン、テトラフェニレン、コラントリレン、ヘリセン、ヘキサフェン、ルビセン、コロネン、トリナフチレン、ヘプタフェン、ピラントレン、フラン、ベンゾフラン、イソベンゾフラン、キサンテン、オキサトレン、ジベンゾフラン、ペリキサンテノキサンテン、チオフェン、チオキサンテン、チアントレン、フェノキサチイン、チオナフテン、イソチアナフテン、チオフテン、チオファントレン、ジベンゾチオフェン、ピロール、ピラゾール、テルラゾール、セレナゾール、チアゾール、イソチアゾール、オキサゾール、フラザン、インドリジン、インドール、イソインドール、インダゾール、プリン、キノリジン、イソキノリン、イミダゾール、ナフチリジン、フタラジン、ベンゾジアゼピン、キノキサリン、シンノリン、キノリン、プテリジン、フェナントリジン、アクリジン、ペリミジン、フェナントロリン、フェナジン、カルボリン、フェノテルラジン、フェノセレナジン、フェノチアジン、フェノキサジン、アンチリジン、ベンゾチアゾール、ベンゾイミダゾール、ベンゾオキサゾール、ベンゾイソオキサゾール、ベンゾイソチアゾール又はこれら芳香環が複数連結された芳香族化合物等からm個のHを取って生じる基が挙げられる。 Specific examples of aromatic hydrocarbon groups or aromatic heterocyclic groups include benzene, pentalene, indene, naphthalene, azulene, heptalene, octalene, indacene, acenaphthylene, phenalene, phenanthrene, anthracene, trindene, fluoranthene, acephenanthrylene, aceanthrylene, triphenylene, pyrene, chrysene, tetraphene, tetracene, pleiadene, picene, perylene, pentaphene, pentacene, tetraphenylene, cholanthrylene, helicene, hexaphene, rubicene, coronene, trinaphthylene, heptaphene, pyranthrene, furan, benzofuran, isobenzofuran, xanthene, oxatrene, dibenzofuran, peri-xanthenoxanthene, thiophene, thioxanthene, thianthrene, phenoxathiin, thionaphthene, and isothianaphthene. , thiophthene, thiophanthrene, dibenzothiophene, pyrrole, pyrazole, tellurazole, selenazole, thiazole, isothiazole, oxazole, furazan, indolizine, indole, isoindole, indazole, purine, quinolizine, isoquinoline, imidazole, naphthyridine, phthalazine, benzodiazepine, quinoxaline, cinnoline, quinoline, pteridine, phenanthridine, acridine, perimidine, phenanthroline, phenazine, carboline, phenotellurazine, phenoselenazine, phenothiazine, phenoxazine, anthridine, benzothiazole, benzimidazole, benzoxazole, benzisoxazole, benzisothiazole, or a group obtained by removing m H atoms from an aromatic compound in which a plurality of aromatic rings are linked together.
なお、連結芳香族基である場合、連結される数は2~10が好ましく、より好ましくは2~7であり、連結される芳香環は同一であっても異なっていても良い。その場合、式(3)中、m個のカルバゾリル基と結合する結合位置は限定されず、連結された芳香環の末端部の環であっても中央部の環であってもよい。ここで、芳香環は芳香族炭化水素環及び芳香族複素環を総称する意味である。In the case of a linked aromatic group, the number of links is preferably 2 to 10, more preferably 2 to 7, and the linked aromatic rings may be the same or different. In that case, the bonding positions of the m carbazolyl groups in formula (3) are not limited, and may be terminal rings or central rings of the linked aromatic rings. Here, aromatic ring is a general term for aromatic hydrocarbon rings and aromatic heterocycles.
上記連結芳香族基の具体例としては、ビフェニル、ターフェニル、クアテルフェニル、ビナフタレン、フェニルトリフェニレン、フェニルジベンゾフラン、フェニルジベンゾチオフェン、ビスジベンゾフラン、ビスジベンゾチオフェン等から水素を除いて生じる基が挙げられる。 Specific examples of the above-mentioned linking aromatic groups include groups generated by removing hydrogen from biphenyl, terphenyl, quaterphenyl, binaphthalene, phenyltriphenylene, phenyldibenzofuran, phenyldibenzothiophene, bisdibenzofuran, bisdibenzothiophene, etc.
好ましいL7の具体例は、ベンゼン、ナフタレン、アントラセン、ビフェニル、ターフェニル、ジベンゾフラン、ジベンゾチオフェン、フェニルジベンゾフラン、又はフェニルジベンゾチオフェンから生じる基が挙げられる。より好ましくは、ベンゼン、ビフェニル、又はターフェニルから生じる基が挙げられる。 Preferred specific examples of L7 include groups derived from benzene, naphthalene, anthracene, biphenyl, terphenyl, dibenzofuran, dibenzothiophene, phenyldibenzofuran, or phenyldibenzothiophene. More preferred are groups derived from benzene, biphenyl, or terphenyl.
mは1~3の整数を表す。好ましくはmは1又は2であり、より好ましくは1である。
nは繰り返し数であり、それぞれ独立して1~4の整数を表す。好ましくはnは1~3である。しかし、少なくとも1つのnは2~4の整数である。
m represents an integer of 1 to 3. Preferably, m is 1 or 2, and more preferably 1.
n is a repeating number and each occurrence is independently an integer from 1 to 4. Preferably, n is an integer from 1 to 3. However, at least one occurrence of n is an integer from 2 to 4.
一般式(4)において、式中に少なくとも1つの式(c1)又は式(c2)で表される結合構造を有することが好ましい。カルバゾリル基間の全ての結合構造が式(c1)、又は式(c2)で表される結合構造であることが、より好ましい。
nの総和(カルバゾリル基の総数)は2~12の整数であるが、好ましくは2~9であり、より好ましくは2~6である。
In the general formula (4), it is preferable that the formula has at least one bond structure represented by formula (c1) or formula (c2). It is more preferable that all the bond structures between the carbazolyl groups are bond structures represented by formula (c1) or formula (c2).
The sum of n (the total number of carbazolyl groups) is an integer of 2 to 12, preferably 2 to 9, and more preferably 2 to 6.
一般式(4)、式(c1)、式(c2)において、R13はそれぞれ独立して水素、炭素数1~10のアルキル基又は炭素数3~11のシクロアルキル基を表す。好ましくは水素、炭素数1~8のアルキル基又は炭素数3~8のシクロアルキル基であり、より好ましくは水素、炭素数1~4のアルキル基又は炭素数5~7のシクロアルキル基である。 In general formula (4), formula (c1), and formula (c2), R 13 each independently represents hydrogen, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 11 carbon atoms. Preferably, R 13 represents hydrogen, an alkyl group having 1 to 8 carbon atoms, or a cycloalkyl group having 3 to 8 carbon atoms, and more preferably, R 13 represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 7 carbon atoms.
アルキル基の具体例としては、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基が挙げられ、好ましくはメチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基が挙げられる。上記アルキル基は直鎖であっても、分岐していても構わない。 Specific examples of alkyl groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups, and preferably methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl groups. The alkyl groups may be linear or branched.
シクロアルキル基の具体例としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基、メチルシクロヘキシル基が挙げられ、好ましくはシクロヘキシル基、メチルシクロヘキシル基が挙げられる。 Specific examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and methylcyclohexyl groups, and preferably cyclohexyl and methylcyclohexyl groups.
一般式(4)で表されるカルバゾール化合物の具体例を以下に示すが、これらに限定されるものではない。 Specific examples of carbazole compounds represented by general formula (4) are shown below, but are not limited to these.
次に、上記一般式(5)について説明する。
一般式(5)において、環Dは式(5a)で表される複素環であり、環Dは隣接する環と任意の位置で縮合する。
R14~R16は独立に水素、重水素、炭素数1~10の脂肪族炭化水素基、炭素数6~30の芳香族炭化水素基又は炭素数3~12の芳香族複素環基である。これらの脂肪族炭化水素基、芳香族炭化水素基又は芳香族複素環基は、一般式(3)のR10~R12がこれらの基である場合と同じであり、好ましい範囲も同様である。
L8は独立に単結合、炭素数6~10の芳香族炭化水素基又はそれらが2~10連結してなる連結芳香族基である。これらの芳香族炭化水素基は、一般式(3)のL6がこれらの基である場合と同じであり、好ましい範囲も同様である。
Ar2は炭素数6~30の芳香族炭化水素基である。芳香族炭化水素基の例は、一般式(4)のL7がこれらの基である場合と同じであり、好ましい範囲も同様である。
i、j、kは、各々独立して0~3の整数を表す。
Next, the above general formula (5) will be described.
In general formula (5), ring D is a heterocycle represented by formula (5a), and ring D is fused to the adjacent ring at any position.
R to R 16 are independently hydrogen, deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or an aromatic heterocyclic group having 3 to 12 carbon atoms. These aliphatic hydrocarbon groups, aromatic hydrocarbon groups, and aromatic heterocyclic groups are the same as when R to R 12 in general formula ( 3 ) are these groups, and the preferred ranges are also the same.
L8 is independently a single bond, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or a linked aromatic group formed by linking 2 to 10 of these groups. These aromatic hydrocarbon groups are the same as those when L6 in general formula (3) is these groups, and the preferred ranges are also the same.
Ar2 is an aromatic hydrocarbon group having a carbon number of 6 to 30. Examples of the aromatic hydrocarbon group are the same as those when L7 in general formula (4) is these groups, and the preferred ranges are also the same.
i, j, and k each independently represent an integer of 0 to 3.
一般式(5)で表されるインドロカルバゾール化合物の具体例を以下に示すが、これらに限定されるものではない Specific examples of the indolocarbazole compound represented by general formula (5) are shown below, but are not limited to these.
前記一般式(1)で表される化合物から選ばれる第1ホストと前記一般式(2)、(3)、(4)又は(5)で表される化合物から選ばれる第2ホストを発光層のホスト材料として使用することで優れた有機EL素子を提供することができる。An excellent organic EL element can be provided by using a first host selected from the compounds represented by the general formula (1) and a second host selected from the compounds represented by the general formula (2), (3), (4) or (5) as the host material of the light-emitting layer.
第1ホストと第2ホストは、個々に異なる蒸着源から蒸着して使用することもできるが、蒸着前に予備混合して予備混合物とし、その予備混合物を1つの蒸着源から同時に蒸着して発光層を形成することが好ましい。この場合、予備混合物には、発光層を形成するために必要な発光性ドーパント材料又は必要により使用される他のホストを混合させてもよいが、所望の蒸気圧となる温度に大きな差がある場合は、別の蒸着源から蒸着させることがよい。Although the first host and the second host can be used by being vapor-deposited from different vapor deposition sources, it is preferable to premix them before vapor deposition to form a premixture, and then vapor-deposit the premixture simultaneously from one vapor deposition source to form the light-emitting layer. In this case, the premixture may contain a light-emitting dopant material required to form the light-emitting layer or other hosts to be used as necessary, but if there is a large difference in the temperature at which the desired vapor pressure is achieved, it is preferable to vapor-deposit them from different vapor deposition sources.
また、第1ホストと第2ホストの混合比(重量比)は、第1ホストと第2ホストの合計に対し、第1ホストの割合が20~60%がよく、好ましくは20%よりも多く、55%よりも少ないことであり、より好ましくは40~50%である。 In addition, the mixing ratio (weight ratio) of the first host to the second host is preferably such that the proportion of the first host relative to the total of the first host and the second host is 20 to 60%, preferably greater than 20% and less than 55%, and more preferably 40 to 50%.
次に、本発明の有機EL素子の構造について、図面を参照しながら説明するが、本発明の有機EL素子の構造はこれに限定されない。Next, the structure of the organic EL element of the present invention will be described with reference to the drawings, but the structure of the organic EL element of the present invention is not limited to this.
図1は本発明に用いられる一般的な有機EL素子の構造例を示す断面図であり、1は基板、2は陽極、3は正孔注入層、4は正孔輸送層、5は発光層、6は電子輸送層、7は陰極を表す。本発明の有機EL素子は発光層と隣接して励起子阻止層を有してもよく、また発光層と正孔注入層との間に電子阻止層を有してもよい。励起子阻止層は発光層の陽極側、陰極側のいずれにも挿入することができ、両方同時に挿入することも可能である。本発明の有機EL素子では、陽極、発光層、そして陰極を必須の層として有するが、必須の層以外に正孔注入輸送層、電子注入輸送層を有することがよく、更に発光層と電子注入輸送層の間に正孔阻止層を有することがよい。なお、正孔注入輸送層は、正孔注入層と正孔輸送層のいずれか、または両者を意味し、電子注入輸送層は、電子注入層と電子輸送層のいずれか又は両者を意味する。 Figure 1 is a cross-sectional view showing an example of the structure of a general organic EL element used in the present invention, in which 1 represents a substrate, 2 represents an anode, 3 represents a hole injection layer, 4 represents a hole transport layer, 5 represents an emitting layer, 6 represents an electron transport layer, and 7 represents a cathode. The organic EL element of the present invention may have an exciton blocking layer adjacent to the emitting layer, or may have an electron blocking layer between the emitting layer and the hole injection layer. The exciton blocking layer can be inserted on either the anode side or the cathode side of the emitting layer, or both can be inserted at the same time. The organic EL element of the present invention has an anode, an emitting layer, and a cathode as essential layers, but may have a hole injection transport layer and an electron injection transport layer in addition to the essential layers, and may further have a hole blocking layer between the emitting layer and the electron injection transport layer. The hole injection transport layer means either the hole injection layer or the hole transport layer, or both, and the electron injection transport layer means either the electron injection layer or the electron transport layer, or both.
図1とは逆の構造、すなわち基板1上に陰極7、電子輸送層6、発光層5、正孔輸送層4、陽極2の順に積層することも可能であり、この場合も必要により層を追加、省略することが可能である。
It is also possible to have the opposite structure to that shown in Figure 1, that is, to stack the
―基板―
本発明の有機EL素子は、基板に支持されていることが好ましい。この基板については特に制限はなく、従来から有機EL素子に用いられているものであれば良く、例えばガラス、透明プラスチック、石英等からなるものを用いることができる。
-substrate-
The organic EL element of the present invention is preferably supported by a substrate. There are no particular limitations on the substrate, and any substrate that has been conventionally used for organic EL elements, such as glass, transparent plastic, quartz, etc., can be used.
―陽極―
有機EL素子における陽極材料としては、仕事関数の大きい(4eV以上)金属、合金、電気伝導性化合物又はこれらの混合物からなる材料が好ましく用いられる。このような電極材料の具体例としてはAu等の金属、CuI、インジウムチンオキシド(ITO)、SnO2、ZnO等の導電性透明材料が挙げられる。また、IDIXO(In2O3-ZnO)等の非晶質で、透明導電膜を作成可能な材料を用いてもよい。陽極はこれらの電極材料を蒸着やスパッタリング等の方法により、薄膜を形成させ、フォトリソグラフィー法で所望の形状のパターンを形成しても良く、あるいはパターン精度をあまり必要としない場合(100μm以上程度)は、上記電極材料の蒸着やスパッタリング時に所望の形状のマスクを介してパターンを形成してもよい。あるいは有機導電性化合物のような塗布可能な物質を用いる場合には印刷方式、コーティング方式等湿式成膜法を用いることもできる。この陽極より発光を取り出す場合には、透過率を10%より大きくすることが望ましく、また陽極としてのシート抵抗は数百Ω/□以下が好ましい。膜厚は材料にもよるが、通常10~1000nm、好ましくは10~200nmの範囲で選ばれる。
-anode-
As the anode material in the organic EL element, a material consisting of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a large work function (4 eV or more) is preferably used. Specific examples of such electrode materials include metals such as Au, CuI, indium tin oxide (ITO), SnO 2 , ZnO, and other conductive transparent materials. In addition, amorphous materials such as IDIXO (In 2 O 3 -ZnO) that can form a transparent conductive film may be used. The anode may be formed by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering, and forming a pattern of a desired shape by a photolithography method, or when pattern accuracy is not required very much (about 100 μm or more), a pattern may be formed through a mask of a desired shape during vapor deposition or sputtering of the electrode material. Alternatively, when a coatable material such as an organic conductive compound is used, a wet film formation method such as a printing method or a coating method may be used. When light is to be emitted from this anode, it is desirable to make the transmittance greater than 10%, and the sheet resistance of the anode is preferably several hundred Ω/□ or less. The film thickness varies depending on the material, but is usually selected from the range of 10 to 1000 nm, preferably 10 to 200 nm.
―陰極―
一方、陰極材料としては仕事関数の小さい(4eV以下)金属(電子注入性金属)、合金、電気伝導性化合物又はこれらの混合物からなる材料が用いられる。このような電極材料の具体例としては、ナトリウム、ナトリウム―カリウム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、インジウム、リチウム/アルミニウム混合物、希土類金属等が挙げられる。これらの中で、電子注入性及び酸化等に対する耐久性の点から、電子注入性金属とこれより仕事関数の値が大きく安定な金属である第二金属との混合物、例えばマグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム混合物、リチウム/アルミニウム混合物、アルミニウム等が好適である。陰極はこれらの陰極材料を蒸着やスパッタリング等の方法により薄膜を形成させることにより、作製することができる。また、陰極としてシート抵抗は数百Ω/□以下が好ましく、膜厚は通常10nm~5μm、好ましくは50~200nmの範囲で選ばれる。なお、発光した光を透過させるため、有機EL素子の陽極又は陰極のいずれか一方が透明又は半透明であれば発光輝度は向上し、好都合である。
-cathode-
On the other hand, as the cathode material, a material consisting of a metal (electron injecting metal), an alloy, an electrically conductive compound, or a mixture thereof having a small work function (4 eV or less) is used. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, a magnesium/copper mixture, a magnesium/silver mixture, a magnesium/aluminum mixture, a magnesium/indium mixture, an aluminum/aluminum oxide (Al 2 O 3 ) mixture, indium, a lithium/aluminum mixture, and a rare earth metal. Among these, from the viewpoint of electron injectability and durability against oxidation, etc., a mixture of an electron injecting metal and a second metal having a larger and more stable work function than the electron injecting metal, such as a magnesium/silver mixture, a magnesium/aluminum mixture, a magnesium/indium mixture, an aluminum/aluminum oxide mixture, a lithium/aluminum mixture, and aluminum, is suitable. The cathode can be produced by forming a thin film of these cathode materials by a method such as deposition or sputtering. In addition, the sheet resistance of the cathode is preferably several hundred Ω/□ or less, and the film thickness is usually selected in the range of 10 nm to 5 μm, preferably 50 to 200 nm. In addition, if either the anode or the cathode of the organic EL element is transparent or semi-transparent in order to transmit the emitted light, the luminance of the emitted light is improved, which is advantageous.
また、陰極に上記金属を1~20nmの膜厚で形成した後に、陽極の説明で挙げた導電性透明材料をその上に形成することで、透明又は半透明の陰極を作製することができ、これを応用することで陽極と陰極の両方が透過性を有する素子を作製することができる。In addition, by forming the above metals in a thickness of 1 to 20 nm on the cathode and then forming the conductive transparent material mentioned in the explanation of the anode on top of it, a transparent or semi-transparent cathode can be produced. This can be applied to create an element in which both the anode and cathode are transparent.
―発光層―
発光層は陽極及び陰極のそれぞれから注入された正孔及び電子が再結合することにより励起子が生成した後、発光する層であり発光層には有機発光性ドーパント材料とホストを含む。
-Emitting layer-
The light-emitting layer is a layer that emits light after excitons are generated by recombination of holes and electrons injected from the anode and cathode, respectively, and contains an organic light-emitting dopant material and a host.
ホストには、上記第1ホストと第2ホストを使用する。
第1ホストしての一般式(1)で表される化合物は、1種を使用してもよく、2種以上を使用してもよい。同様に、第2ホストしての一般式(2)~(5)で表されるカルバゾール化合物又はインドロカルバゾール化合物は1種を使用してもよく、2種以上を使用してもよい。
必要により、公知のホスト材料を1種又は複数種類併用しても良いが、その使用量はホスト材料の合計に対し、50wt%以下、好ましくは25wt%以下とすることがよい。
他の材料をホストとして使用してもよい。
As the hosts, the above-mentioned first host and second host are used.
The compound represented by formula (1) as the first host may be used alone or in combination of two or more.Similarly, the carbazole compound or indolocarbazole compound represented by formulas (2) to (5) as the second host may be used alone or in combination of two or more.
If necessary, one or more known host materials may be used in combination, but the amount of such materials used is 50 wt % or less, preferably 25 wt % or less, based on the total amount of the host materials.
Other materials may also be used as the host.
第1ホストと第2ホストは、それぞれ異なる蒸着源から蒸着するか、蒸着前に予備混合して予備混合物とすることで1つの蒸着源から第1ホストと第2ホストを同時に蒸着することもできる。The first host and the second host can be deposited from different deposition sources, or they can be premixed before deposition to form a premixture, allowing the first host and the second host to be deposited simultaneously from a single deposition source.
第1ホストと第2ホストを予備混合して使用する場合は、良好な特性を有する有機EL素子を再現性良く作製するために、50%重量減少温度(T50)の差が小さいことが望ましい。50%重量減少温度は、窒素気流減圧(50Pa)下でのTG-DTA測定において、室温から毎分10℃の速度で550℃まで昇温したとき、重量が50%減少した際の温度をいう。この温度付近では、蒸発又は昇華による気化が最も盛んに起こると考えられる。 When the first host and the second host are premixed and used, it is desirable that the difference in 50% weight loss temperature (T 50 ) is small in order to reproducibly fabricate an organic EL device having good characteristics. The 50% weight loss temperature is the temperature at which the weight is reduced by 50% when the temperature is raised from room temperature to 550°C at a rate of 10°C per minute in TG-DTA measurement under reduced pressure (50 Pa) of nitrogen gas flow. It is considered that vaporization by evaporation or sublimation occurs most actively around this temperature.
第1ホストと第2ホストは、上記50%重量減少温度の差が20℃以内であることが好ましく、15℃以内であることがより好ましい。予備混合方法としては、粉砕混合等の公知の方法が採用できるが、可及的に均一に混合することが望ましい。The difference in the 50% weight loss temperature between the first host and the second host is preferably within 20°C, more preferably within 15°C. As a premixing method, a known method such as grinding and mixing can be used, but it is desirable to mix as uniformly as possible.
発光性ドーパント材料として燐光発光ドーパントを使用する場合、燐光発光ドーパントとしては、ルテニウム、ロジウム、パラジウム、銀、レニウム、オスミウム、イリジウム、白金及び金から選ばれる少なくとも1つの金属を含む有機金属錯体を含有するものがよい。具体的には、J.Am.Chem.Soc.2001,123,4304や特表2013-53051号公報に記載されているイリジウム錯体が好適に用いられるが、これらに限定されない。When a phosphorescent dopant is used as the luminescent dopant material, the phosphorescent dopant is preferably an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, and gold. Specifically, the iridium complexes described in J.Am.Chem.Soc.2001,123,4304 and JP2013-53051A are preferably used, but are not limited to these.
燐光発光ドーパント材料は、発光層中に1種類のみが含有されても良いし、2種類以上を含有しても良い。燐光発光ドーパント材料の含有量はホスト材料に対して0.1~30wt%であることが好ましく、1~20wt%であることがより好ましい。The light-emitting layer may contain only one type of phosphorescent dopant material, or may contain two or more types. The content of the phosphorescent dopant material is preferably 0.1 to 30 wt % of the host material, and more preferably 1 to 20 wt %.
燐光発光ドーパント材料は、特に限定されるものではないが、具体的には以下のような例が挙げられるThe phosphorescent dopant material is not particularly limited, but specific examples include the following:
発光性ドーパント材料として蛍光発光ドーパントを使用する場合、蛍光発光ドーパントとしては、特に限定されないが例えばベンゾオキサゾール誘導体、ベンゾチアゾール誘導体、ベンゾイミダゾール誘導体、スチリルベンゼン誘導体、ポリフェニル誘導体、ジフェニルブタジエン誘導体、テトラフェニルブタジエン誘導体、ナフタルイミド誘導体、クマリン誘導体、縮合芳香族化合物、ペリノン誘導体、オキサジアゾール誘導体、オキサジン誘導体、アルダジン誘導体、ピロリジン誘導体、シクロペンタジエン誘導体、ビススチリルアントラセン誘導体、キナクリドン誘導体、ピロロピリジン誘導体、チアジアゾロピリジン誘導体、スチリルアミン誘導体、ジケトピロロピロール誘導体、芳香族ジメチリジン化合物、8-キノリノール誘導体の金属錯体やピロメテン誘導体の金属錯体、希土類錯体、遷移金属錯体に代表される各種金属錯体等、ポリチオフェン、ポリフェニレン、ポリフェニレンビニレン等のポリマー化合物、有機シラン誘導体等が挙げられる。好ましくは縮合芳香族誘導体、スチリル誘導体、ジケトピロロピロール誘導体、オキサジン誘導体、ピロメテン金属錯体、遷移金属錯体、又はランタノイド錯体が挙げられ、より好ましくはナフタレン、ピレン、クリセン、トリフェニレン、ベンゾ[c]フェナントレン、ベンゾ[a]アントラセン、ペンタセン、ペリレン、フルオランテン、アセナフトフルオランテン、ジベンゾ[a,j]アントラセン、ジベンゾ[a,h]アントラセン、ベンゾ[a]ナフタレン、ヘキサセン、ナフト[2,1-f]イソキノリン、α‐ナフタフェナントリジン、フェナントロオキサゾール、キノリノ[6,5-f]キノリン、ベンゾチオファントレン等が挙げられる。これらは置換基としてアルキル基、アリール基、芳香族複素環基、又はジアリールアミノ基を有しても良い。When a fluorescent dopant is used as the luminescent dopant material, examples of the fluorescent dopant include, but are not limited to, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives, condensed aromatic compounds, perinone derivatives, oxadiazole derivatives, oxazine derivatives, aldazine derivatives, pyrrolidine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, styrylamine derivatives, diketopyrrolopyrrole derivatives, aromatic dimethylidine compounds, various metal complexes such as metal complexes of 8-quinolinol derivatives, metal complexes of pyrromethene derivatives, rare earth complexes, and transition metal complexes, polymer compounds such as polythiophene, polyphenylene, and polyphenylenevinylene, and organic silane derivatives. Preferred are condensed aromatic derivatives, styryl derivatives, diketopyrrolopyrrole derivatives, oxazine derivatives, pyrromethene metal complexes, transition metal complexes, or lanthanoid complexes, and more preferred are naphthalene, pyrene, chrysene, triphenylene, benzo[c]phenanthrene, benzo[a]anthracene, pentacene, perylene, fluoranthene, acenaphthofluoranthene, dibenzo[a,j]anthracene, dibenzo[a,h]anthracene, benzo[a]naphthalene, hexacene, naphtho[2,1-f]isoquinoline, α-naphthalenephenanthridine, phenanthroxazole, quinolino[6,5-f]quinoline, benzothiophanthrene, etc. These may have an alkyl group, an aryl group, an aromatic heterocyclic group, or a diarylamino group as a substituent.
蛍光発光ドーパント材料は、発光層中に1種類のみが含有されても良いし、2種類以上を含有しても良い。蛍光発光ドーパント材料の含有量は、ホスト材料に対して0.1~20%であることが好ましく、1~10%であることがより好ましい。The light-emitting layer may contain only one type of fluorescent dopant material, or two or more types. The content of the fluorescent dopant material is preferably 0.1 to 20% of the host material, and more preferably 1 to 10%.
発光性ドーパント材料として熱活性化遅延蛍光発光ドーパントを使用する場合、熱活性化遅延蛍光発光ドーパントとしては、特に限定されないがスズ錯体や銅錯体等の金属錯体や、WO2011/070963号公報に記載のインドロカルバゾール誘導体、Nature 2012,492,234に記載のシアノベンゼン誘導体、カルバゾール誘導体、Nature Photonics 2014,8,326に記載のフェナジン誘導体、オキサジアゾール誘導体、トリアゾール誘導体、スルホン誘導体、フェノキサジン誘導体、アクリジン誘導体等が挙げられる。When a thermally activated delayed fluorescent dopant is used as the luminescent dopant material, examples of the thermally activated delayed fluorescent dopant include, but are not limited to, metal complexes such as tin complexes and copper complexes, indolocarbazole derivatives described in WO2011/070963, cyanobenzene derivatives and carbazole derivatives described in Nature 2012,492,234, phenazine derivatives, oxadiazole derivatives, triazole derivatives, sulfone derivatives, phenoxazine derivatives, and acridine derivatives described in Nature Photonics 2014,8,326, and the like.
熱活性化遅延蛍光発光ドーパント材料は、特に限定されるものではないが、具体的には以下のような例が挙げられる。 The thermally activated delayed fluorescent dopant material is not particularly limited, but specific examples include the following:
熱活性化遅延蛍光発光ドーパント材料は、発光層中に1種類のみが含有されてもよいし、2種類以上を含有してもよい。また、熱活性化遅延蛍光発光ドーパントは燐光発光ドーパントや蛍光発光ドーパントと混合して用いてもよい。熱活性化遅延蛍光発光ドーパント材料の含有量は、ホスト材料に対して0.1~50%であることが好ましく、1~30%であることがより好ましい。The light-emitting layer may contain only one type of thermally activated delayed fluorescent dopant material, or may contain two or more types. The thermally activated delayed fluorescent dopant may be mixed with a phosphorescent dopant or a fluorescent dopant. The content of the thermally activated delayed fluorescent dopant material is preferably 0.1 to 50% and more preferably 1 to 30% of the host material.
-注入層-
注入層とは、駆動電圧低下や発光輝度向上のために電極と有機層間に設けられる層のことで、正孔注入層と電子注入層があり、陽極と発光層又は正孔輸送層の間、及び陰極と発光層又は電子輸送層との間に存在させてもよい。注入層は必要に応じて設けることができる。
- Injection layer -
The injection layer is a layer provided between an electrode and an organic layer to reduce the driving voltage and improve the luminance of light emitted, and includes a hole injection layer and an electron injection layer, and may be provided between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer. The injection layer can be provided as necessary.
-正孔阻止層-
正孔阻止層とは広い意味では電子輸送層の機能を有し、電子を輸送する機能を有しつつ正孔を輸送する能力が著しく小さい正孔阻止材料からなり、電子を輸送しつつ正孔を阻止することで発光層中での電子と正孔の再結合確率を向上させることができる。
-Hole blocking layer-
A hole blocking layer, in a broad sense, has the function of an electron transport layer and is made of a hole blocking material that has the function of transporting electrons but has an extremely low ability to transport holes, and by transporting electrons while blocking holes, it is possible to improve the probability of recombination of electrons and holes in the light-emitting layer.
正孔阻止層には、公知の正孔阻止層材料を用いることができるが、一般式(1)で表される化合物を含有させることが好ましい。The hole blocking layer may be made of any known hole blocking layer material, but it is preferable to incorporate a compound represented by general formula (1).
-電子阻止層-
電子阻止層とは広い意味では正孔輸送層の機能を有し、正孔を輸送しつつ電子を阻止することで発光層中での電子と正孔が再結合する確率を向上させることができる。
-Electron blocking layer-
In a broad sense, the electron blocking layer functions as a hole transport layer, and can increase the probability of recombination of electrons and holes in the light emitting layer by blocking electrons while transporting holes.
電子阻止層の材料としては、公知の電子阻止層材料を用いることができ、また後述する正孔輸送層の材料を必要に応じて用いることができる。電子阻止層の膜厚は好ましくは3~100nmであり、より好ましくは5~30nmである。As the material for the electron blocking layer, a known electron blocking layer material can be used, and the material for the hole transport layer described later can also be used as necessary. The thickness of the electron blocking layer is preferably 3 to 100 nm, more preferably 5 to 30 nm.
-励起子阻止層-
励起子阻止層とは、発光層内で正孔と電子が再結合することにより生じた励起子が電荷輸送層に拡散することを阻止するための層であり、本層の挿入により励起子を効率的に発光層内に閉じ込めることが可能となり、素子の発光効率を向上させることができる。励起子阻止層は2つ以上の発光層が隣接する素子において、隣接する2つの発光層の間に挿入することができる。
-Exciton blocking layer-
The exciton blocking layer is a layer for preventing excitons generated by the recombination of holes and electrons in the light-emitting layer from diffusing into the charge transport layer, and the insertion of this layer makes it possible to efficiently confine excitons in the light-emitting layer, thereby improving the luminous efficiency of the device. In a device having two or more adjacent light-emitting layers, the exciton blocking layer can be inserted between two adjacent light-emitting layers.
励起子阻止層の材料としては、公知の励起子阻止層材料を用いることができる。例えば、1,3-ジカルバゾリルベンゼン(mCP)や、ビス(2-メチル-8-キノリノラト)-4-フェニルフェノラトアルミニウム(III)(BAlq)が挙げられる。The material for the exciton blocking layer can be any known exciton blocking layer material, such as 1,3-dicarbazolylbenzene (mCP) or bis(2-methyl-8-quinolinolato)-4-phenylphenolatoaluminum(III) (BAlq).
-正孔輸送層-
正孔輸送層とは正孔を輸送する機能を有する正孔輸送材料からなり、正孔輸送層は単層又は複数層設けることができる。
-Hole transport layer-
The hole transport layer is made of a hole transport material having a function of transporting holes, and the hole transport layer may be provided as a single layer or multiple layers.
正孔輸送材料としては、正孔の注入又は輸送、電子の障壁性のいずれかを有するものであり、有機物、無機物のいずれであってもよい。正孔輸送層には従来公知の化合物の中から任意のものを選択して用いることができる。かかる正孔輸送材料としては例えば、ポルフィリン誘導体、アリールアミン誘導体、トリアゾール誘導体、オキサジアゾール誘導体、イミダゾール誘導体、ポリアリールアルカン誘導体、ピラゾリン誘導体及びピラゾロン誘導体、フェニレンジアミン誘導体、アリールアミン誘導体、アミノ置換カルコン誘導体、オキサゾール誘導体、スチリルアントラセン誘導体、フルオレノン誘導体、ヒドラゾン誘導体、スチルベン誘導体、シラザン誘導体、アニリン系共重合体、また導電性高分子オリゴマー、特にチオフェンオリゴマー等が挙げられるが、ポルフィリン誘導体、アリールアミン誘導体及びスチリルアミン誘導体を用いることが好ましく、アリールアミン化合物を用いることがより好ましい。The hole transport material is one that has either hole injection or transport or electron barrier properties, and may be either organic or inorganic. Any of the conventionally known compounds can be selected and used for the hole transport layer. Examples of such hole transport materials include porphyrin derivatives, arylamine derivatives, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline-based copolymers, and conductive polymer oligomers, particularly thiophene oligomers, etc., but it is preferable to use porphyrin derivatives, arylamine derivatives, and styrylamine derivatives, and it is more preferable to use arylamine compounds.
-電子輸送層-
電子輸送層とは電子を輸送する機能を有する材料からなり、電子輸送層は単層又は複数層設けることができる。
-Electron transport layer-
The electron transport layer is made of a material having a function of transporting electrons, and the electron transport layer may be provided as a single layer or as a multi-layer.
電子輸送材料(正孔阻止材料を兼ねる場合もある)としては、陰極より注入された電子を発光層に伝達する機能を有していればよい。電子輸送層には、従来公知の化合物の中から任意のものを選択して用いることができ、例えば、ナフタレン、アントラセン、フェナントロリン等の多環芳香族誘導体、トリス(8-キノリノラート)アルミニウム(III)誘導体、ホスフィンオキサイド誘導体、ニトロ置換フルオレン誘導体、ジフェニルキノン誘導体、チオピランジオキシド誘導体、カルボジイミド、フルオレニリデンメタン誘導体、アントラキノジメタン及びアントロン誘導体、ビピリジン誘導体、キノリン誘導体、オキサジアゾール誘導体、ベンゾイミダゾール誘導体、ベンゾチアゾール誘導体、インドロカルバゾール誘導体等が挙げられる。更にこれらの材料を高分子鎖に導入した、又はこれらの材料を高分子の主鎖とした高分子材料を用いることもできる。The electron transport material (which may also serve as a hole blocking material) may have the function of transmitting electrons injected from the cathode to the light emitting layer. For the electron transport layer, any of the conventionally known compounds may be selected and used, such as polycyclic aromatic derivatives such as naphthalene, anthracene, and phenanthroline, tris(8-quinolinolato)aluminum(III) derivatives, phosphine oxide derivatives, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, bipyridine derivatives, quinoline derivatives, oxadiazole derivatives, benzimidazole derivatives, benzothiazole derivatives, and indolocarbazole derivatives. Furthermore, polymeric materials in which these materials are introduced into the polymer chain or in which these materials are the main chain of the polymer may also be used.
以下、本発明を実施例によって更に詳しく説明するが、本発明はこれらの実施例に限定されるものではなく、その要旨を超えない限りにおいて、種々の形態で実施することが可能である。The present invention will now be described in more detail with reference to examples, but the present invention is not limited to these examples and can be implemented in various forms without departing from the spirit of the invention.
実施例1
膜厚110nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-5Paで積層した。まず、ITO上に正孔注入層としてHAT-CNを25nmの厚さに形成し、次に正孔輸送層としてNPDを30nmの厚さに形成した。次に電子阻止層としてHT-1を10nmの厚さに形成した。次に、第1ホストとして化合物1-1を、第2ホストとして化合物2-4を、発光ドーパントとしてIr(ppy)3をそれぞれ異なる蒸着源から共蒸着し、40nmの厚さに発光層を形成した。この時、Ir(ppy)3の濃度が10wt%、第1ホストと第2ホストの重量比が30:70となる蒸着条件で共蒸着した。次に電子輸送層としてET-1を20nmの厚さに形成した。更に電子輸送層上に電子注入層としてLiFを1nmの厚さに形成した。最後に、電子注入層上に、陰極としてAlを70nmの厚さに形成し、有機EL素子を作製した。
Example 1
On a glass substrate on which an anode made of ITO with a film thickness of 110 nm was formed, each thin film was laminated at a vacuum degree of 4.0×10 −5 Pa by vacuum deposition. First, HAT-CN was formed on ITO to a thickness of 25 nm as a hole injection layer, and then NPD was formed to a thickness of 30 nm as a hole transport layer. Next, HT-1 was formed to a thickness of 10 nm as an electron blocking layer. Next, compound 1-1 was co-deposited as a first host, compound 2-4 was co-deposited as a second host, and Ir(ppy) 3 was co-deposited as an emitting dopant from different deposition sources to form an emitting layer with a thickness of 40 nm. At this time, the co-deposition was performed under deposition conditions where the concentration of Ir(ppy) 3 was 10 wt%, and the weight ratio of the first host to the second host was 30:70. Next, ET-1 was formed to a thickness of 20 nm as an electron transport layer. Furthermore, LiF was formed to a thickness of 1 nm on the electron transport layer as an electron injection layer. Finally, an Al film was formed as a cathode with a thickness of 70 nm on the electron injection layer to complete the organic EL device.
実施例1~88
実施例1において、第1ホスト及び第2ホストを、表1、2に示す化合物を使用した以外は実施例1と同様にして有機EL素子を作製した。
Examples 1 to 88
An organic EL device was prepared in the same manner as in Example 1, except that the compounds shown in Tables 1 and 2 were used as the first host and the second host.
実施例89~96
第1ホスト及び第2ホストを事前に混合して予備混合物とした後、これを一つの蒸着源から共蒸着した。
実施例1において、第1ホスト(0.30g)と第2ホスト(0.70g)を量りとり、乳鉢ですり潰しながら混合することにより得た予備混合物を使用した以外は実施例1と同様にして有機EL素子を作成した。
Examples 89 to 96
The first host and the second host were mixed in advance to prepare a premixture, which was then co-deposited from one deposition source.
An organic EL device was prepared in the same manner as in Example 1, except that a preliminary mixture was prepared by weighing out the first host (0.30 g) and the second host (0.70 g) and mixing them while grinding them in a mortar.
作製した有機EL素子の評価結果を表1~4に示す。
表中で輝度、駆動電圧、発光効率は駆動電流20mA/cm2時の値であり、初期特性である。LT70は、初期輝度が70%まで減衰するまでにかかる時間であり、寿命特性を表す。
The evaluation results of the prepared organic EL devices are shown in Tables 1 to 4.
In the table, the brightness, driving voltage, and luminous efficiency are values at a driving current of 20 mA/ cm2 , which are initial characteristics. LT70 is the time it takes for the initial brightness to decay to 70%, and indicates the life characteristics.
比較例1
実施例1において、ホストとして化合物1-1を単独で用いた以外は実施例1と同様にして有機EL素子を作製した。発光層の厚み、発光ドーパント濃度は実施例1と同様である。
Comparative Example 1
An organic EL device was produced in the same manner as in Example 1, except that Compound 1-1 was used alone as the host in Example 1. The thickness of the light-emitting layer and the concentration of the light-emitting dopant were the same as in Example 1.
比較例2~15
ホストとして表5に示す化合物を単独で用いた以外は比較例1と同様にして有機EL素子を作製した。
Comparative Examples 2 to 15
An organic EL device was prepared in the same manner as in Comparative Example 1, except that a compound shown in Table 5 was used alone as the host.
比較例16~24
実施例1において、第1ホストとして化合物Aを使用し、第2ホストとして化合物2-5、化合物2-6、化合物3-24、化合物3-33、化合物3-45、化合物4-3、化合物4-22、化合物5-3又は化合物5-19を使用した以外は実施例1と同様にして有機EL素子を作製した。
Comparative Examples 16 to 24
An organic EL device was produced in the same manner as in Example 1, except that Compound A was used as the first host and Compound 2-5, Compound 2-6, Compound 3-24, Compound 3-33, Compound 3-45, Compound 4-3, Compound 4-22, Compound 5-3 or Compound 5-19 was used as the second host.
比較例25~33
比較例16~24において、第1ホストとして化合物Bを使用した以外は比較例16~24と同様にして有機EL素子を作製した。
Comparative Examples 25 to 33
In Comparative Examples 16 to 24, organic EL devices were prepared in the same manner as in Comparative Examples 16 to 24, except that Compound B was used as the first host.
比較例34~42
比較例16~24において、第1ホストとして化合物Cを使用した以外は比較例16~24と同様にして有機EL素子を作製した。
Comparative Examples 34 to 42
In Comparative Examples 16 to 24, organic EL devices were prepared in the same manner as in Comparative Examples 16 to 24, except that Compound C was used as the first host.
作製した有機EL素子の評価結果を表5~6に示す。The evaluation results of the fabricated organic EL elements are shown in Tables 5 and 6.
表1~4から実施例1~96は、電力効率及び寿命特性が向上し、良好な特性を示すことが分かる。 From Tables 1 to 4, it can be seen that Examples 1 to 96 have improved power efficiency and life characteristics and exhibit good characteristics.
実施例97
膜厚110nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-5Paで積層した。まず、ITO上に正孔注入層としてHAT-CNを25nmの厚さに形成し、次に正孔輸送層としてNPDを45nmの厚さに形成した。次に、電子阻止層としてHT-1を10nmの厚さに形成した。次に、第1ホストとして化合物1-1を、第2ホストとして化合物2-4を、発光ドーパントとしてIr(piq)2acacをそれぞれ異なる蒸着源から共蒸着し、40nmの厚さに発光層を形成した。この時Ir(piq)2acacの濃度が6.0wt%となる蒸着条件で共蒸着した。次に電子輸送層としてET-1を37.5nmの厚さに形成した。そして電子輸送層上に電子注入層としてLiFを1nmの厚さに形成した。最後に、電子注入層上に、陰極としてAlを70nmの厚さに形成し、有機EL素子を作製した。
Example 97
On a glass substrate on which an anode made of ITO with a thickness of 110 nm was formed, each thin film was laminated at a vacuum degree of 4.0×10 −5 Pa by vacuum deposition. First, HAT-CN was formed to a thickness of 25 nm as a hole injection layer on ITO, and then NPD was formed to a thickness of 45 nm as a hole transport layer. Next, HT-1 was formed to a thickness of 10 nm as an electron blocking layer. Next, compound 1-1 was co-deposited as a first host, compound 2-4 was co-deposited as a second host, and Ir(piq) 2 acac was co-deposited as an emitting dopant from different deposition sources to form an emitting layer with a thickness of 40 nm. At this time, the co-deposition was performed under deposition conditions where the concentration of Ir(piq) 2 acac was 6.0 wt%. Next, ET-1 was formed to a thickness of 37.5 nm as an electron transport layer. Then, LiF was formed to a thickness of 1 nm as an electron injection layer on the electron transport layer. Finally, an Al film was formed as a cathode with a thickness of 70 nm on the electron injection layer to complete an organic EL device.
実施例98~182
実施例97において、第1ホスト及び第2ホストを、表7~9に示す化合物を使用した以外は実施例97と同様にして有機EL素子を作製した。
Examples 98 to 182
An organic EL device was prepared in the same manner as in Example 97, except that the compounds shown in Tables 7 to 9 were used as the first host and the second host.
作製した有機EL素子の評価結果を表7~9に示す。ここで、LT95は、初期輝度が95%まで減衰するまでにかかる時間であり、寿命特性を表す。The evaluation results of the fabricated organic EL elements are shown in Tables 7 to 9. Here, LT95 is the time it takes for the initial luminance to decay to 95%, and indicates the life characteristics.
比較例43
実施例97において、ホストとして化合物1-1を単独で用いた以外は実施例97と同様にして有機EL素子を作製した。発光層の厚み、発光ドーパント濃度は実施例97と同様である。
Comparative Example 43
An organic EL device was produced in the same manner as in Example 97, except that Compound 1-1 was used alone as the host in Example 97. The thickness of the emitting layer and the concentration of the emitting dopant were the same as in Example 97.
比較例44~57
ホストとして表10に示す化合物を単独で用いた以外は比較例43と同様にして有機EL素子を作製した。
Comparative Examples 44 to 57
An organic EL device was prepared in the same manner as in Comparative Example 43, except that a compound shown in Table 10 was used alone as the host.
比較例58~66
実施例97において、第1ホストとして化合物Aを、第2ホストとして化合物2-5、化合物2-6、化合物3-24、化合物3-33、化合物3-45、化合物4-3、化合物4-22、化合物5-3又は化合物5-19を使用した以外は実施例97と同様にして有機EL素子を作製した。
Comparative Examples 58 to 66
An organic EL device was prepared in the same manner as in Example 97, except that Compound A was used as the first host and Compound 2-5, Compound 2-6, Compound 3-24, Compound 3-33, Compound 3-45, Compound 4-3, Compound 4-22, Compound 5-3 or Compound 5-19 was used as the second host.
比較例67~75
比較例58~66において、第1ホストとして化合物Bを使用した以外は比較例58~66と同様にして有機EL素子を作製した。
Comparative Examples 67 to 75
In Comparative Examples 58 to 66, organic EL devices were prepared in the same manner as in Comparative Examples 58 to 66, except that Compound B was used as the first host.
比較例76~84
比較例58~66において、第1ホストとして化合物Cを使用した以外は比較例58~66と同様にして有機EL素子を作製した。
Comparative Examples 76 to 84
In Comparative Examples 58 to 66, organic EL devices were prepared in the same manner as in Comparative Examples 58 to 66, except that Compound C was used as the first host.
作製した有機EL素子の評価結果を表10~11に示す。The evaluation results of the prepared organic EL elements are shown in Tables 10 and 11.
表7~9から実施例97~182は、電力効率及び寿命特性が向上し、良好な特性を示すことが分かる。 From Tables 7 to 9, it can be seen that Examples 97 to 182 have improved power efficiency and life characteristics and exhibit good characteristics.
実施例で使用した化合物を次に示す。
本発明の有機EL素子は、低電圧で駆動可能で、高効率、長寿命を達成できる。
The organic EL device of the present invention can be driven at a low voltage and can achieve high efficiency and a long life.
Claims (10)
第1ホストは下記一般式(1)で表される化合物から選ばれ、
第2ホストは下記一般式(2)又は一般式(4)で表される化合物から選ばれることを特徴とする有機電界発光素子。
The first host is selected from compounds represented by the following general formula (1):
An organic electroluminescent device, wherein the second host is selected from the compounds represented by the following general formula (2) or (4):
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